Sail with me, Dean Winchester
by monkeysknees
Summary: In which Castiel is a navy captain, Dean is a pirate, and a mysterious drifting ship changes their lives forever. [Castiel/Dean] possible later sabriel.
1. Chapter 1

-1-

The wind whipped into his face, spraying ocean water on it as Castiel stood on the bowof his ship. The Geogiana tipped and swayed in the sea. It was a windy day, so his ship was making steady headway on it's journey to drop off supplies to a navy port. Castiel's crew bustled about him. They were 4 days from port, and most of them were becoming restless, wanting to spend at least one day on shoreleave. As the mist cooled his face, he let a small trace of a smile play across his features. This was where he belonged.

Supply runs like these usually only took a couple of weeks, but Castiel had been given a special mission. Not only was he to diliver some special secret cargo to the largest and most important navy port on the eastern seaboard, but he also had the privelige of making one of the longest and hardest trips available for a captain as of little importance as himself.

He puffed his chest up a little as he thought of how important his task was. He hadn't been told what the cargo was or why it was so imperative that it be protected at all costs, but he knew that he had been specially selected for the job.

Michael had summoned him particularly because, frankly, his ships was one of the least important in the fleet, and the most likely to be ignored by roaming scumbags and pirates.

He had been promised that if he succeeded in this mission, that he would be awarded a raise, and a new ship. While The Georgiana was a sturdy ship, and hadn't given him many problems, it was still small, and traveled much slower than many of its cousins in the fleet.

"Sir reaching 60 knots, we're still against the current, and the wind seems to be changing directions again. This could set us back at least a week. What do you say?" Castiel's first mate aproached him.

"Turn to starboard and sail into the wind. I know this area well. If we detour slightly east we'll be able to skirt this current and at least make it in a week." Castiels gruff, low voice caried over the sound of waves hitting the hull, and wind flapping in the sails.

The crewman nodded and headed back to the navigator, shouting instructions at a few men here and there.

Castiel didn't mind. He trusted his crew more or less. His first mate could get bossy, but he always confered with Castiel before doing anything, let alone giving out orders. Plus it gave him time to think. There was nothing Castiel loved more than standing at the bow of his ship, feeling the wind in his hair, thinking.

Many years ago, when he was just starting to learn the trade of the sea to become a merchant like his father, Castiel was walking through a busy port and came across an old man. He was talking animatedly to a group of sailors who were all inthralled. He spoke of a man. Castiel had nudged closer, trying to hear all the details. Apparently the subject at matter was rather exciting. A young man had just been promoted to admiral. The youngest admiral in history, actually. He was apparently fast becoming infamous at bustling ports. He sailed the finest ship in the navy, second only to the great Michael. He was extremely handsome and could take on 5 fully grown men once, though he was very young and still growing. Castiel stood at awe in the stories. He decided then to change his trade. He joined the navy, if only for a chance of a glimpse at the famous Dean Winchester.

That was before the war of course. Before the greatest test the navy had ever experienced. Castiel heard many stories when he was just a lowly sailor. He mostly listened, and stored the stories away to anylise later. Then when the war happened, the stories became more serious, more solemn. Rumors of a brother gone astray, of a deal with davy jones himself, then his famed disappearence. Nobody knew what happened to him. They'd assumed he'd been captured. All they really knew was that as soon as Winchester disappeared, the war stopped. The pirates just simply stopped attacking. It seemed they had completed their purpose. Dean Winchester wasn't heard from for two years. Most people said he was dead. Then he mysteriously appeared in a port one day, a pirate port mind you, wearing dark tattered clothing, heavily armed, and followed by the most allusive of pirates. He quickly sailed to the top of the most wanted list. First anitiative for the navy was to capture Dean Winchester.

It was Castiel's dream; Capture Dean Winchester, the man he'd been obsessing over for a large portion of his life. It was daunting, sure. Winchester was described as being 3 heads above all men, large in stature, almost completely muscle, with a beard to rival all beards, and a nasty scar aross his face, mutilating it almost beyond recognition. And if the legends meant anything, he could take on 10 men drunk and blindfolded.

But Castiel wasn't worried. He was clever, and strong, and what he lacked in bulk, he more than made up for in strategy.

"Captain, ship spotted off stern!" A shout from the mast snapped Castiel out of his reverie.

"Colors" Castiel shouted back

"It appears to fly under the flag of a merchant, sir"

Castiels first mate appeared at his side. "This is rare for these waters, sir. Shall we approach and ask their business?"

Castiel simply nodded. He didn't see the harm in it. Often times, merchants would even slip him a treat, if he noticed something against code. Who could say no to a spice cake after weeks on hard tack?

The Georgiana cut through the water, heading swiftly toward the ship in the distance, with help from a steady brease that helpfully filled its sails.

As his ship approached, however, Castiel sensed something was off. He cracked open his telescope and got a closer look at the ship. His suspiciouns were merited. There was no one on her deck. She appeared to be drifting, empty.

"Balthazar, come here." Castiel called to his first mate.

"Yes sir?"

"The ship appears to be empty," he told Balthazar, "It could be a trap. But there could still be someone on her that may need our assistance. We do have... important cargo. Should we risk it?"

Balthazar looked through the looking glass. "Sir, we're already on course. If there are people aboard that ship waiting to ambush us, we could hardly avoid it at this point. And of course, we can't report to the Navy that we saw a mysterious abandoned ship, and just let it drift away without further investigation."

"Very well," Castiel nodded. It's what he'd thought as well. But Balthazar was a good first mate, and generally he took his advice seriously. "We shall see."

The crew held their breath as the Georgiana aproached the drifting vessel.


	2. Chapter 2

**-2-**

The abandoned ship creaked in the wind. Its side had the name "Indigo" written on it in peeling blue letters. The crew of the Georgiana boarded the Indigo with uncertainty. There was something eerie in the air; Castiel felt it as he stepped onto the hull of the other ship; something softly telling him to stop, to turn back. But he kept walking because something deeper, whether it was a sense of curiosity or some strange sixth sense, was telling him to keep going. That it mattered, this strange lonely abandoned ship.

It looked like it had been there for a while. The deck was well weathered, to the point of muffling the sailors' footsteps. Castiel's eyes fell to the captain's quarters, which looked like it had been abandoned for some time. In fact, the whole ship seemed to be strangely empty. He reasoned that there must have been a terrible storm that blew all the supplies over deck. But the sails were huge and pristine, perfectly white and billowing in the air, though the ship wasn't moving as it should have been. The merchant flag flew on the mast, proud and perfectly intact. The ship gave a presence as if it had been there a long time, but had never been encountered before.

"McCoy and Adams, check below deck." Castiel ordered. His voice, usually strong and commanding, sounded muffled in the strange air.

"Sir," The taller one, McCoy said, "are you sure this is a good idea? I have an odd feeling about this place. It doesn't seem right."

"McCoy, do as you're told. Don't make me ask again. Check below deck." Castiel growled.

McCoy and the other one, Adams, looked at each other nervously and made their way down below to the bowels of the Indigo.

"Ingot, Carply, Hancock and Smith," he picked out a few reliable men, "check the deck for any signs of recent habitation." The group nodded and set to work.

"The rest of you head back to the Georgiana. We set back to sea within the hour." A dozen or so haphazard crew headed back to their ship, happy to get off the Indigo and her weathered floors.

"Balthazar, Come with me." Castiel walked to the captain's quarters with Balthazar beside him.

"What say you? Is this a ship out of a story? Did I forget to wake up this morning?" Balthazar joked halfheartedly.

"I assure you, Balthazar, you are awake. This ship appears to be real, although by all accounts it makes no sense."

As Balthazar rolled his eyes at Castiel, the latter was busy checking the captains quarters. In one corner was a rolltop desk, empty except for a stack of blank white paper waiting to be written on. On the far wall was a large table with a map of the whole coast stretching across it. It had been painted on, and there were holes where pins must have previously been. A large bed sat in the middle of the room, and took up a sizable amount of space in the cramped captain's quarters. It had no matrice, just a frame, although the frame was gorgeous and appeared to be made of some sort of mahogany and expertly crafted. Castiel ran his hand along one of the bed posts as he walked to the table.

"This ship can't seem to make up its mind." Balthazar commented, eyeing the bed, "I can't decide if it's meant for a king or a pirate."

"It would appear that whoever used this last, they had an exquisite taste in the finer things, and yet would be happy to live in a dump." Castiel said. He was both impressed and disgusted. No doubt he could do a better job running this ship than the last person had. If there had been a last person. It looked like the boat had never been used, like some great wild untamed horse, waiting for a master and carer to groom it into domestication.

"What's this?" Balthazar asked of the map.

"A map." Castiel said, tilting his head quizzically at him, wondering why he would ask such a stupid question.

"I can see that, sir. I was more specifically referring to the perfectly charted currents and winds." His finger traced a current all the way to where they were now, in the middle of a strange circle where many different current converged and met in one spot. "This is odd. I hadn't heard the currents did this..." as his finger tapped the mysterious spot, a loud boom sounded from outside.

Castiel whipped around. There were shouts from his crew. "We're being ambushed." he growled at Balthazar. He drew his sword and flew out the door of the captain's quarters.

Outside was quite a sight. The Georgiana, which was anchored next to the indigo, was alit with a fiery blaze. Rowdy, tattered pirates were hopping from their ship, a rotting old master cruiser with molded sails, a holey hull, and black flag. Castiels crew had their hands full putting out the blaze, as well as fighting off the new arrivals. Some had started boarding the Indigo. Balthazar drew his sword and charged at the intruders. Castiel flew towards his ship, his mind on one thing: the special cargo.

As he crossed the plank onto his own ship, dodging brawls in order to get below the deck, he cursed his stupidity. He had been given a mission. He had to protect the cargo at all costs. The navy relied on it. If anything happened to it, he would be ruined, yes, but it could potentially harm thousands of innocent people. Though the fire was spreading, he ran as fast as he could, below the deck. sifting through the piles of wreckage, undoubtedly caused by the pirates, Castiel drew towards the gunpowder room. He opened the door and stepped inside the room. It was filled with barrels of gunpowder for the cannons. He had to work fast, or he would be blown to smithereens. He approached one of the barrels and dug his hand into the gunpowder. Fishing out a small box, he placed it in the breast pocket of his tan overcoat.

Shouts were heard from above, and Castiel knew he had to make his getaway. The number one rule of the Navy was "A captain must go down with his ship", but his instructions told him that he must protect the special cargo with his, his crew's, and his ship's lives. That meant if he had to abandon his crew and his ship to bring the cargo to safety, then that was what he must do.

Opening the door from the armory, Castiel peeked out to see a roaring fire. He wouldn't be able to pass through there, and he only had a small amount of time before the fire would spread to the gunpowder. He had one choice, open the small window and try to squeeze out of the ship into the water below. Castiel winced. It was cold outside. Last night the spray from the ocean had frozen to the railings on the Georgiana. He wasn't looking forward to this.

Castiel pushed a barrel up to the window and pried it open with his hands. It was a hard job, as the window hadn't been opened in years, most likely, and was rusted shut. Ignoring the pain in his fingers he slowly pulled the old metal hatch open and squeezed through the small window. It took some effort, but he managed to slip out, legs first. He held onto the windowsill looking down at the water below. This was going to hurt. He let go and fell into the water below him. The freezing salty water swallowed him up. As he resurfaced, he heard the sound of his beautiful ship, the Georgiana, exploding.

The Georgiana was a thing of beauty, even as she sank below the waves, laying pirate and sailor alike to rest. The dark blue water, still as eerie and calm as it was when they approached the indigo, gurgled where his ship had been. He felt a knot in his stomach knowing that all he had in his life had just been gobbled up by the sea.

Above him, the Indigo still sat calmly in the water. Her head was held high, and she seemed somehow undisturbed by the artillery and fighting happening around her. So much so that Castiel was once again drawn to her. He swam to the ship and found a rope there, hanging over the edge as if it were waiting for him. He grabbed onto it and began the arduous task of lifting himself out of the sea and into the ship. Though his hands burned by the time he made it to the deck, he had no time to linger on it. A pirate came up from behind him swinging his sword high above his head.

Castiel drew his sword in the nick of time. His sword clanged loudly as it collided with the pirate's.

"A thousand curses to you!" Castiel growled at the pirate as he ran him through with his sword.

Everything he had worked for, everything that he had wanted to be had been destroyed and ruined because of these pirates. He had nothing now. So he did what he did best, fighting his way through the crowd of barbarians.

His dramatic conquests must have drawn the attention of the pirates for they started crying for their captain. Castiel looked up from the corpse he had just made. Many of his men lay dead on the deck. But some were still fighting. He saw young Marian taking on three men nearly twice his size at once, and managing quite well. Amid his anger and grief he felt a sense of pride for this young man. He was his favorite pupil. At the far end of the ship near the helm, he saw Balthazar fighting a huge pirate. The pirate stood taller than everyone else, and had flowing long brown hair. A small, mousy looking pirate near Castiel was calling for the captain, cowering as Castiel drew near him.

As Castiel drew his sword to slaughter the pirate, another one came from his left and jumped in front of the smaller pirate. Castiel didn't have any time to look at the pirate, but from what he could tell, the man was around his height, maybe taller, and looked extremely angry. Castiel aimed all his attention towards his new assailant. The man drew his sword and stalked towards Castiel. The two circled each other for a bit before the pirate made the first move. He thrust his sword at Castiel's right side. As Castiel blocked his blow, he managed to strike to the right. The man was fast. Deadly fast. Castiel hopped onto a nearby barrel to give himself the upperground. He hurt his agility to dodge most of the pirate's strikes.

His agility wasn't the only thing he was using against the pirate. He was trying to move the two towards the edge of the boat. The all he would have to do is push the pirate overboard to be rid of him. But the pirate's strikes were fast and swift. He hadn't managed to so much as put a cut on Castiel, but each of his blows were getting closer, as if the longer he fought with Castiel, the better he knew how to defeat him.

A shout went up from the other side of the ship. The pirate and Castiel both turned towards it, pausing in their great battle. Balthazar and the man he was fighting were still in an intense fight, but another pirate had joined in. He was short, especially compared to the large man standing next to him, but he seemed to be extremely cunning. They had Balthazar on his knees, his sword laying several feet away from him.

Castiel heard a chuckle escape from the pirate standing next to him and he took the opportunity to try to disarm him. He was quick, however, and his sword, rather than being knocked from his hands, was once again being struck in Castiel's direction. A smirk was playing across the pirate's features.

"I don't think I've ever fought someone by the likes of you." The pirate growled. His voice was low and gravelly.

"I practice." was Castiel's wordy retort.

The pirate laughed at this. His head threw back and his body shook. This perplexed Castiel, who lowered his sword. An opponent laughing at him? The best swordsman in the navy?

"I do believe I've met my match." The pirate said. He lowered his sword. "I guess this is why you bring a gun to a swordfight." From his coat he pulled a winchester rifle. He pointed it directly at Castiel's head.

"I wouldn't try moving if I were you." He growled, low and menacing.

* * *

><p><em>Hello, Folks. Good to see you here reading my story. This is the first fanfic I've ever written, so keep that in mind when you're judging it. ;) I hope you enjoyed this chapter. I published the last one incorrectly accidently. I posted the unedited version so sorry about all the mistakes. I'm gonna fix that now. <em>

_Please review so I can hear your thoughts!_

_If you want, you can also follow me on tumblr - .com _

_I'm also working on opening an etsy shop in which I will sell various supernatural items, but more on that later. _

_Thanks for reading! -monkeysknees._


	3. Chapter 3

**-3-**

The man who had his gun pointed at Castiel was much cleaner cut than the pirates Castiel was accustomed to seeing. Most of the pirates that Castiel had seen, mostly being escorted to the gallows at a navy port, had long, matted, dirty hair. But this man's hair was short, light colored and looked decently clean. Other than a light shadow clinging to his jaw, he was clean shaven. Castiel saw a glint of mischievous green eyes behind the gun pointed at his face. The pirate was wearing a dark outfit, his sword was held forgotten in his left hand. In his right hand was that magnificent winchester rifle. It gleamed in the afternoon sun. Obviously, it was a prize of a possession, and was polished regularly. The pirate gestured to the scraggly boards of the Indigo with his gun.

"On your knees, twinkle toes."

Castiel knelt. He instinctively backed away when the pirate reached for him.

"Relax. I'm just gonna see what it is you're hiding so well from us." Cooed the pirate. His hands reached for Castiel's coat and felt the lump that Castiel had been hoping, praying, would be ignored.

"Ah. What's this?" The pirate said.

"It's none of your business," Castiel spat "I would appreciate it if you took your filthy hands off me."

The pirate tsked, reached inside Castiel's coat, and withdrew the box. It was a dark wooden box, and on it was a carving of two hands intertwined. It was nailed shut. Castiel had been told that he must not, under any circumstances, open it or allow it to be opened.

"What have we here?" The pirate growled. "Sam!" he shouted down the deck.

"Yes, captain?" The large pirate with the long hair shouted back.

Captain. So this was this captain of the pirate crew. It seemed obvious to Castiel as to why. He was the best swordsman Castiel had ever fought against, and he had a commanding air to him, as if he knew how to make anyone respect him. Castiel found himself wondering if this pirate crew managed more crime than the average. They seemed organized. He looked down the deck, where the pirate was looking. His men were being captured and held by the pirates. Many were already being escorted onto the adjacent pirate ship. Sam, the large pirate, was helping the small pirate next to him tie Balthazar's hands together.

"Come here!" The man ordered.

Sam let go of Balthazar, left the small pirate to escort the struggling sailor onto the pirate ship, and trotted over. Once the larger pirate had joined him, the captain said "Grab his hands. We're keeping this one in this ship. The Indigo is her name, right? Lets put him in the captain's quarters. I'll need to keep an eye on him to make sure he doesn't run off before we've... talked to him."

The pirate said all this quietly to Sam, but Castiel still heard. Sam nodded and grabbed Castiel's arms, kicking his sword away. As soon as the gun was lowered, Castiel naturally struggled. He needed to free his men. Sure the Georgiana was sunken, but he could make his escape in this strange mystery ship. But Sam's grip was too strong, and Castiel found himself in the captain's quarters of the Indigo, separated from his crew.

The shorter pirate followed Sam and Castiel into the room. "That bed needs a matrice," he nodded to the frame, "Go get one from my chambers, will ya? I have an extra. And bring us some bread and cheese."

The large man made a face at his captain. "You forgot the magic word." he said.

"Go or I'll tie your arms and legs together and have you thrown overboard." The pirate menaced.

Sam rolled his eyes and left, closing the door behind him. Castiel found this behavior strange. This captain must be very close to his crew in order for him to stand being talked to like that. If one of Castiel's crew acted like that, he would serve strict punishment, and most likely be disbanded at the next port.

The pirate gestured at one of the chairs at the table, indicating that Castiel should sit in it. Castiel merely crossed his arms and glared at him.

"Come on. You must be tired after all that. I know I am. Have a seat."

Castiel continued to glare.

"We aren't going to get anywhere fast if you act like that." the pirate goaded at Castiel.

Castiel did not respond.

"Alright. Have it your way." He pulled out his gun and pointed it at Castiel's head. "Sit down or I'll blow your brains out." he said lightly.

Finally Castiel stalked slowly over to the table and sank into the chair. The pirate walked over and traced his fingers over the map, stopping at the place where the currents converged.

"So this is where we are now, huh?" he said to himself "Explains the calm waters."

Castiel glared up at the pirate, who remained standing.

"Speaking of which, you must be freezing. You're soaking wet. I'll have sam bring over some fresh clothes."

Indeed Castiel was freezing. The sea water was extremely cold that day. It was a wonder it wasn't frozen to him because of the cold air. Dry clothes would be amazing in contrast to his dripping ones, but he wasn't about to let it show.

The pirate looked up from the map at Castiel, stood up to his full height and put on an air of command.

"Well enough chit chat. Lets get down to it, shall we?" he said "What is this ship? Have you ever heard of it?"

Castiel glared up at him for a few seconds, then gave up and sighed. "This ship is called the Indigo. It was why we anchored here. It was just floating there. It has a merchant flag, so I decided to inspect it, but as you can see, the place is abandoned."

"Was there anyone on board when you arrived? Or any evidence that someone was on board recently?" The pirate shifted so he was leaning against the bed frame, his arms crossed in a way that made his arm muscles bulge. It definitely added to the intimidation factor.

"There was strangely no sign that anyone has ever used this ship at any point." Castiel admitted before adding "Well, up until our battle. Now it's a graveyard for many good men." Castiel glared at the pirate.

"My deepest regrets for your lost sailors, captain. I did what I had to do." the pirate offered

"Killing innocent men? That's what you had to do?" Castiel questioned the man, his voice rising.

"They were not innocent. None of you are." he growled back.

Castiel tilted his head. What could he mean? Had he or his crew done something wrong?

Sam opened the door to the captains quarters. He had a platter full of cheese and bread, and even some ale. Behind him, two pirates carried a mattress.

"Come in." The captain said to his crew members.

Sam carried the platter to the table and set it and a bottle of ale in front of Castiel. The other two pirates carried the mattress over and plopped it onto the bed. It was an old lumpy mattress, complete with stains, and it looked absurd in the beautiful bed frame.

"Do you need anything else?" Sam asked.

"Actually, could you bring this man some dry clothing? He will hardly be any use to us if he's dying of cold" the pirate responded. "Other than that, we're fine. You may leave. This captain and I have much to discuss. But come back in an hour or two, so we can talk a plan."

Sam once again nodded and exited the room with the two pirates.

Once Sam had left, the pirate turned to Castiel again. "You know what you're doing." he growled at Castiel, all prior friendliness replaced with venom. "You know what you are."

"I honestly have no idea what you're speaking of," Castiel replied, head still tilted, "Me and my crew are good men. We defend the seas from roaming scumbags like yourself who do nothing but spread fear and steal property."

The pirate laughed, but this laugh wasn't like the last, which shook his body; this laugh didn't even reach his eyes. It was humourless and sarcastic.

"You really don't know?" the man said, shaking his head, "You just take orders like a dog, vying for your master's attention and praise. I should have known. You military men are all the same. You think you're completing some holy mission. That you are saviors. You never wonder if you're as good as you originally supposed."

He uncrossed his arms, walked over to the table and sat across from Castiel. Out of his pocket he pulled the small box. He placed it on the table, in between Castiel and himself.

"Do you have any idea what this is?" he asked seriously, searching Castiel's eyes for an answer.

"I.." Castiel hesitated, wondering how much he should say.

The pirate sighed. "I know about the secret mission, so you can stuff it on the innocent act."

"It is not my place to disclose any information about this... box." Castiel said, his voice low, steady.

"Of course it isn't. Well let's start over here. What is your name?" the man asked, sitting back in his chair.

Castiel merely stared quizzically at him.

"Look, we're gonna be here awhile. Might as well get acquainted. So. What is your name, captain?"

Castiel looked up at the man. He was watching Castiel from across the table, one eyebrow cocked. The late afternoon sun was streaming through the portals in the hull of the ship, illuminating this man's eyes. Where before they seemed to have a mysterious glint, they now had a fiery quality to them. The man was waiting for an answer.

"Castiel." he let out. His voice was quiet. "Castiel." He said again, this time stronger, more commanding.

"Castiel. Cas. Listen, Cas." Castiel flinched at the shortening of his name "I know neither of us want this to take long. We both have our respected business to attend to. Now I don't know what your business is but," he reached across the table and grabbed a piece of bread off the untouched platter "mine is to make sure that that," he gestured at the box with the bread in his hand "doesn't get wherever it is that you're taking it."

"It would seem our missions are counteractive, then." Castiel said.

"It would seem." he replied.

Castiel watched as the pirate sat back in his chair and took a large bite out of the bread. He was looking at Castiel, his eyebrows raised. There was a small silence as the man ate his bread. He seemed to be waiting for Castiel to speak. Castiel refused to speak first.

Finally, once he had finished he slice of bread, he pointed to the platter of bread and cheese. "You gonna eat that?" he asked

Castiel merely pushed the platter towards him. But he kept the ale.

The silence continued as the pirate ate. Castiel watched in fascination. It looked like he hadn't eaten for days, and the simple snack was a feast for him.

"You know," he said between bites, "You can ask me anything and I'll tell you all I know." he tempted.

Castiel knew this ploy. Trying to gain the trust of the detainee. "You are a pirate." Castiel said after a few moments of consideration.

"Thank you for informing me. I hadn't heard" the pirate said back.

At the lack of any response from the captain, the man said "I'm a pirate. Yes. Pirates steal and cheat and we do kill if merited. But we do not lie."

"You could be lying right now," Castiel pointed out the obvious loophole.

He chuckled at that, his eyes glinting at Castiel ."Trust me, Cas. I'm not lying."

Castiel squinted his eyes at the man across the table, thinking. "How do you know about the... box?" he finally asked.

"I know most things the Navy is up to." the pirate replied. "That..." He nodded at the box "is a big deal, to say the least. So naturally I heard about it."

"How?" Castiel asked again

"I have my sources." the pirate replied. Maybe he wasn't a lying man, but he was allusive. Castiel knew that he wouldn't get far with that line of questions. He thought more.

"Why is your crew insubordinate?" Castiel asked after some time.

The pirate barked out a laugh, not expecting that question.

"You try teaching manners to a group of rowdy pirates sometime. There's a reason they became what they are, and it's to get away from you stiff necks." he pointed at Castiel, "I personally don't like to walk around with a stick in my ass. It's uncomfortable."

Castiel frowned at the sudden change in the mood of the pirate. He seemed to be able to switch from jesting to serious in a manner of seconds. He shook his head and tried to think of another question.

"Is the large man, Sam, your first mate?" Castiel asked.

"Come on, Cas. You're avoiding the question." the pirate said back.

Castiel tilted his head. Had the pirate asked him a question? "What question?"

"The question you should be asking." The pirate said. At Castiel's blank look he continued. "The biggest question in the room. The one you're dying to know the answer to, but you're too afraid to ask. The question that is keeping you sitting at this table on your own free will, even though I'm stuffing my face and clearly unarmed."

Castiel looked to the door. It had occurred to him that he could get up and make his escape, but...

He looked up at the man sitting across the table, tilted his head. Should he ask?

Castiel took a deep breath and opened his mouth.

"What's in the box?"


	4. Chapter 4

_Hello! Sorry this took so long to update. I got a little distracted and busy and what not. This chapter was hard for me to write, and I'm a little eh about it, but hopefully you like it. _

_Anyway enough from me for now. I'll talk to you at the end of the chapter. Read on! _

* * *

><p><strong>-4-<strong>

"What's in the box?" Castiel asked, his eyes moving from the pirate to the small wooden box in the middle of the table.

A smirk played across the pirate's face. He reached over and picked it up. "Well I'm glad you asked. See that's the one thing that I've been wondering myself." he stood up and walked to the door "I'll be right back."

As soon as the pirate left, Castiel reached across the table and picked up the box. It was the same as it was when Castiel put it in his jacket, but now as he held it it felt strange. Somehow it was heavier now. Just how important was this cargo? He glanced at the door. He could leave. He could get up and make his escape. Surely the guard at the door was no match for him. But he found that he didn't want to leave. He wanted to know what was in the box. He wanted to know why the pirates hadn't just killed him. He wanted to know what the navy was up to and why he hadn't thought to question them before. So he waited, sitting at the table, gazing at the small box.

A few minutes later, the pirate came back with the monster pirate, Sam, and a metal bar.

"Lets crack her open." the shorter pirate said.

Sam tossed Castiel some dry clothes. "Put these on. They're dry and you must be freezing."

The pirate captain looked up from the table where he was working at prying open the box, "Yeah can't deal with another body on our hands. Plus you might have information."

Sam rolled his eyes at his captain.

The secret cargo made a noise as the lid moved slightly. Castiel and Sam drew their attention to the box. It seemed to be nailed tightly shut, if the way the pirate was struggling to pry the lid off was any indicator.

"Sammy a little help here." the man said. He was breathing heavily from his struggles.

Sam went over to the pirate and grabbed the little cargo. Together, he and the pirate captain pushed and pulled and pried until the lid came flying off. It sped through the air, coming to rest clattering on the floor on the other side of the cabin where it lay forgotten. All attention was on the contents of the box, which lay in Sam's overly sized paws for hands.

Castiel drew close, tilting his head in confusion. "A key?" why was this so important? What did it open?

"A key." The pirate echoed. "A key, Sammy. What say you?"

Castiel looked up at Sam. He held the box in his hands, examining the small key within it. Sam's eyebrows were creased in his concentration. He seemed to be putting the pieces of a puzzle together in his mind. The other pirate, however, merely seemed grimly amused. He was perched on the edge of the table, arms crossed, looking at Sam.

"A key. Why? That doesn't..." Sam started, placing the box on the table, "Wait... unless" he stuttered, looking at the pirate for confirmation. "no... really?"

The captain nodded and looked, finally, at Castiel. "Well Cas. Maybe you can help us. You know anything about what this means?"

Castiel looked from the pirate to Sam and back in disbelief. "You're jesting."

Sam merely raised an eyebrow.

"You know more than I do! I've made it clear repeatedly that I'm a pawn in this. I have no idea what that key is or what it does. I have no idea what the navy's plan here is. I have no idea what _your _plan is. The both of you know more than I do!" He breathed heavily looking between the two pirates, "I can't believe any of this. I have no idea what's going on, and I can't possibly offer any information on something I know nothing about!"

As he finished his outburst, Castiel collapsed into one of the chairs, his head in his hands. He was in a state of disbelief. None of this seemed remotely real. He had no reason to, but he found himself trusting these men. These pirates. He felt a hand on his back and heard a man clear his throat.

"Uh. Listen... sir." it was Sam. "I understand this must be a little overwhelming for you."

"A little?" Castiel said, looking up from his hands.

"Alright. A lot. Very overwhelming. But we promise that we're the good guys in this. You're going to have to trust us."

Castiel glared up at Sam. The first mate back away a little and looked pleadingly at his captain.

The captain raised his eyebrows to which Sam nodded and shrugged his shoulders, an unspoken communication passing between the captain and his crewman. Turning back to Castiel the pirate said "Here is what's going to happen. You have questions. We're willing to answer them. Me and Sammy are going to sit here and we're going to tell you everything we know because we need your help." The captain sat down in the other chair, facing Castiel while Sam perched on the mattress of the bed.

Castiel looked at the two of them. He seemed to be weighing the two men, trying to see whether he should trust them. They merely looked back, waiting for him to respond. Finally he sighed and sat up straight in his chair. "You want me to question you." he stated. It wasn't a question. It was a statement.

The pirates exchanged a glance. "Uh yeah that's what we just said..." Sam said."

"Well let's start with this. How did you become pirates?"

"You want to know our story?" the captain chuckled, "Well I guess it'll explain a lot." he looked from Castiel to Sam. "You wanna start Sammy?"

"Um sure." Sam said. "Well first things first... we were born in Alexander Colony, a few miles from the cost in Massachusetts."

"We?" Castiel asked, looking between the two men.

"Yeah both of us. We're brothers. He's older." He gave a sidelong glance at his brother who nodded for him to continue. "Our mother died when I was a baby from pirate attacks." Castiel raised his eyebrows at this. "Yes it's a strange parallel. I'll get to that though. Our father, John, he was obsessed with pirates after that. He went a little insane trying to hunt down the crew that murdered our mother. He.. uh trained us from a young age to be fighters. Our father got his own ship in the navy, and took us aboard when we were very small... I must have been, what four?" He looked at his brother for confirmation."

"Yeah that sounds about right. I was eight so you must have been four." the older pirate said. "The point is we were very young when we first set to sea. Our father was very.. ambitious. He wanted us to become the best."

"He was obsessed with it." the younger brother continued, "He gave us fighting lessons every night. He wasn't a very good captain. He loved his spirits and would often times become seriously drunk. And when that happened, he would go crazy."

"One time he forced me to fight him when he was drunk. I refused to because he was not in his right mind, so he came after me with a dagger." the older man interjected, pulling up the sleeve of his shirt. "That's where I got this." He put his arm on the table for Castiel to see. His arm had a long scar extending from his wrist to his elbow.

Castiel was appalled at the scar, thinking the man's own father did this to him.

"He wasn't drink too often though," Sam said, "When we really depended on him, when we needed him most he was there for us."

"Yeah his was a piss for father," the older man said, "but he was a good man in the end. He died saving us. We got jumped in a navy port by some bum, and our father just jumped out and took the blow."

"After that, we had nowhere to go, no one to run to. So we enlisted in the navy ourselves. We were too young, but they made an exception for us because they knew us I suppose. We were put on the ship of a man named Robert Singer. He was like a second father to us. Tought us everything we know about sailing and tracking."

"He retired pretty soon though, so they gave his ship to us. Me and my brother." The older pirate grinned at his brother who rolled his eyes.

"They made Dean the captain and me the first mate. We made a pretty good team, even though I was only... god I must have been 12." He screwed his face up a little, "We were so young and so small. I have no idea what the Navy was thinking. But we did make a good team. We successfully stopped around eight raids in just a short year. And then Michael heard of us."

"Michael?" Castiel asked.

"It was just his first year as the gun ho leader of the navy," the older pirate said. "He had heard of us and decided to meet with us. He talked to us in separate rooms, and before we knew it, he had us separated. I got to talk to Sammy before I left for good, but he had assigned us different positions. Sam was a crewman on some no-name's crappy ship, and I got to be one of Michael's advisors on his ship." he looked up at Sam, who nodded for him to continue.

"From then on out, I was Michael's favorite. I got promoted quickly. Never heard from Sam though. Just four years later, when I was 21, I got a letter saying he had been killed in a raid. Damn right tore me to pieces. Michael told me to channel that energy into my work. So I did.

Then, as you probably know, the war broke out. It was insane. I had so many things to do, so many orders to give, so many fights to fight, but I threw myself into it and I didn't even care about the consequences." he looked up at Castiel,

"This is where it gets interesting." He said, a wry grin spreading across his face.

"So all the fighting and warring it all leads up to this one point. I'm on Michael's ship. I think it was for a strategic meeting or something. Out of the blue, a pirate ship just shows up, and it starts shooting at us. pirates were boarding everywhere. It was a mess. I'm fighting my heart out, giving it all I got, and then all of a sudden, who shows up but Sammy here?" he said, gesturing wildly to Sam.

"He was fighting really well. Better than I'd ever seen him. And I had seen him fight quite a bit. So I made my way over to him and it took him at least a minute to recognize me." He smirked a little at that memory, "He was stunned. Probably not the best place to be stunned, but he just stood there and then pulled me into the biggest bear hug I'd ever had. So we started fighting shoulder to shoulder. Only we were fighting different sides, so he was taking down pirates and I was taking down sailors. I'm sure we looked like complete idiots.

It took a while, but the fighting finally stopped. Michael managed to come up to us and he gave us a choice. Sort of an us or them choice. And I said that I would stay with my crew or die. So it all came down to Dean. And he chose me."

"Proudest moment of my life." The older man rolled his eyes. "We were going to be executed the next day, but we escaped. So I was a pirate. A fugitive of the law. It took some getting used to. But after a while I managed to earn the trust of a few good men. And we started our own crew. And look at us now. Interrogating low level Navy captains with apparently no information."

Sam shot his brother an exasperated look. "The point is, I had left the navy when I was 17. I had learned of some information that the Navy was planning on burning some cities full of people. They were going to blame it on pirates and 'save the day' in order to meet some sort of ridiculous quota. So I left. I spent a good year in a pirate port, working at a pub. Then Gabriel showed up and got me hired on a friend's ship. When the war broke out, the ship I was on was sent in to deliver the final blow." Sam stood up from his seat on the bed and stretched his back.

"So that's our story. Impressed?" the older pirate said, unable to keep the biting sarcasm out of his voice.

Castiel looked between the two men, his eyes wide. How on earth had he managed to meet the two most notorious pirates on the high seas and not even realise it? He had met the man he'd been obsessed with his entire life and he never even suspected it.

"Dean? You are Dean Winchester." he deadpanned.

"At your service." the man, Dean, said back.

* * *

><p><em>Hello again! Thank you for reading my story :) If you like it, please review so I can have motivation to continue. <em>

_This chapter was mostly dialog and filler background story, which is interesting but not as fun to write so it took me a while. The next chapter will be a little more talking and some other stuff as Dean and Sam and Cas will work out the navy's secret plans. Then I PROMISE the plot will move along in chapter 6. Like as in more action. _

_Around chapter nine the destiel will pick up a bit more if you're waiting for that. This fic is a bit more plot centric, but it'll come don't worry._

_Why am I telling you this. This is classified information. _

Thanks for reading! -monkeysknees (danceofthecucumbers on tumblr)


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